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In which of the following compounds is t...

In which of the following compounds is there the least delocalization of the lone pair of electrons on the nirtogen atom?

A

B

C

D

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The correct Answer is:
D
Steric inhibition to resonance due to lack of planarity of nitrogen with aromatic ring. This occur due steric crowding by the three bulky adjacent groups.
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All aliphatic amines are more basic than ammonia but due to delocalization of lone pair of electrons of the nitrogen atom on the benzene ring, aniline is a weaker base than ammonia. The basic strength of the substituted anilines, however, depends upon the nature of the substituent. Whereas electron-donating groups tend to increase, electron-withdrawing groups tend to decrease the basic strength. The base strengthening effect of the electron-donating groups and base weakening effect of the electron-withdrawing groups is, however ,more pronounced at p-than at m-position. However, due to ortho effect, o-substituted anilines are weaker bases than anilines regardless of the nature of substituent whether electron-donating or electron-withdrawing. Among the following, the weakest base is

All aliphatic amines are more basic than ammonia but due to delocalization of lone pair of electrons of the nitrogen atom on the benzene ring, aniline is a weaker base than ammonia. The basic strength of the substituted anilines, however, depends upon the nature of the substituent. Whereas electron-donating groups tend to increase, electron-withdrawing groups tend to decrease the basic strength. The base strengthening effect of the electron-donating groups and base weakening effect of the electron-withdrawing groups is, however ,more pronounced at p-than at m-position. However, due to ortho effect, o-substituted anilines are weaker bases than anilines regardless of the nature of substituent whether electron-donating or electron-withdrawing. Arrange the following amines in decreasing order of their basic strength

All aliphatic amines are more basic than ammonia but due to delocalization of lone pair of electrons of the nitrogen atom on the benzene ring, aniline is a weaker base than ammonia. The basic strength of the substituted anilines, however, depends upon the nature of the substituent. Whereas electron-donating groups tend to increase, electron-withdrawing groups tend to decrease the basic strength. The base strengthening effect of the electron-donating groups and base weakening effect of the electron-withdrawing groups is, however ,more pronounced at p-than at m-position. However, due to ortho effect, o-substituted anilines are weaker bases than anilines regardless of the nature of substituent whether electron-donating or electron-withdrawing. What is the order of basicity of I. p-methylaniline II. m-methylaniline III, aniline IV. o-methylaniline

Which of the following is least basic?

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